This invention relates to a process for the preparation of unsaturated primary amines from the corresponding secondary and tertiary amines.
Allylamine is probably the most useful of the unsaturated primary amines to which the invention relates since it is a valuable intermediate in the production of a number of pharmaceuticals, herbicides and plastics.
One of the problems in the production of primary amines is that almost invariably, unless produced by the reduction of a cyanide group, they are not obtained pure but in substantial admixture with secondary and tertiary amines. In fact, most frequently secondary and tertiary amines form the bulk of the production.
The present invention provides an efficient and convenient means for converting the secondary and tertiary amines into primary amines.
One solution to this problem involves disproportionation of the secondary amine to primary and tertiary amines. Thus U.S. Pat. No. 3,865,877 discloses disproportionating diallylamine to monallylamine and tri-allylamine.
Another method disclosed in an article in Ang. Chem. Int. Edit, 12, p928 (1973), shows the reaction of triallylamine with formic acid to give allyl formate, diallylamine, monoallylamine, propane and carbon monoxide. This is, however, a most uneconomic route since the by-products are many and predominant.
It is, therefore, clear that a process for converting secondary and tertiary unsaturated amines to the monounsaturated amine would be a very useful addition to the art.